Judd Apatow Wants to Make the Real World as Nice as His Movies

May 27, 2015

Two and a half years ago, Judd Apatow released This Is 40, the most personal film of his career. He was anxious. He usually is. His default setting is inward panic.

“I don’t know if people can understand the pressure to be funny,” Apatow says today, “just knowing how badly you can fail and how embarrassing it will be.”

To the public, Apatow had nothing to fear. He was the king of comedy, the overlord of an unprecedented seven-year, 21-film barrage of hits and near-hits that he’d either directed, written, or produced. His leading men had become marquee names: Will Ferrell, Steve Carell, Seth Rogen, Jonah Hill, James Franco, Jason Segel, Russell Brand, Paul Rudd. And Bridesmaids had recently given him his biggest box office haul ever.

But Apatow is fueled by his obsession with flopping. “I work hard and I’m pretending to be positive,” he admits. “In my head, I’m not positive at all.”

Like the George Bailey of comedy, Apatow is less aware of his successes than of his stumbles: the stand-up career he abandoned 25 years ago at age 22, when he realized his roommate, Adam Sandler, was the funny one; the collapse of The Ben Stiller Show, which took him a decade to recover from; the quick and cruel cancellations of Freaks and Geeks and Undeclared — his one-two Hiroshima and Nagasaki, after which he swore off making television and dedicated himself to film.

Today, Apatow has a therapist and a hypnotherapist, and even so, he jokes that when crossing a busy street he speed-walks as if pleading to the impatient drivers, “Please don’t hate me, I’m a good guy, if you knew me you’d like me, I’ll never see you again but your approval is vital to me!”

For Apatow, This Is 40 was the end of an era that began with The 40-Year-Old Virgin and Knocked Up and had christened him, for better or worse, the Lord of the Dudebros. He had become the paterfamilias of 21st-century comedy — and his movie man-children were graduating. Rogen and Franco would go on to form their own clans. Hill would earn two Oscar nominations. Segel would stake a claim with Sundance indies. Rudd would star in a Marvel superhero movie. Apatow’s film family — the one he’d held together for twelve years — was splintering.

Adding to the pressure, This Is 40 not only was a story about his marriage, it starred his wife, Leslie Mann, and two daughters, Maude and Iris, and even squeezed in a cameo for his 90-year-old grandmother. Awaiting the reviews, his guilt was intense. If people didn’t like it, they weren’t just rejecting him — they were vetoing his actual family.

Part of the problem is that This Is 40 is too honest about Apatow’s life. He set the film in a house not too different from his current L.A. home, a kid-perfect oasis with three dogs, two tree swings, and one angora rabbit. Though the film is devastatingly direct about the frustrations of marriage — few comedies can successfully depict the nice guy, in this case Rudd, wishing his wife would “just, like, drift into a coma, from which she never awakens” — the posh digs made his characters look like ingrates. Apatow had priced himself out of the audience’s empathy, even though the couple’s fumbling selfishness was precisely his point.

“It’s almost like a therapy session to write these movies,” he says. “I covered a lot of ground. I did a show about high school, college, people who just got out of college, getting married, kids, being a comedian, sickness, death, financial problems, long-term relationships.” With This Is 40, he’d finally caught up to his present. There was nothing left to say.

So Apatow stopped writing film scripts. Not only personal films, all films. He attempted to write a play, then put it away. He researched a couple other theater ideas, “but I never landed on something that I thought would work.”

What now?

Maybe it was time to let other people speak.

When Apatow was a teenage comedy fan, all he did was listen. At sixteen, he hosted a radio show called Comedy Club at his Syosset, Long Island, high school. His mother, Tamara, worked at an actual comedy club, and the show was Apatow’s excuse to hang out at her job and wheedle Jerry Seinfeld and Garry Shandling into hour-long sit-down interviews, filing away all their advice until he was ready to take the mic himself his senior year.

Apatow dug out his tapes of those 30-year-old chats to hear what spoke to him now. He’s older than Seinfeld and Shandling were then, and in those three decades fame had changed all of their lives. He decided to turn his archive of
interviews into a book, Sick in the Head: Conversations About Life and Comedy, out this June.

The book also includes Q&As with two of his most famous muses: Rogen, the
unknown Canadian kid whom Apatow built into a multiplex megastar, and Lena Dunham, the princess of HBO, whose $45,000 indie film Tiny Furniture so impressed him that he emailed her out of the blue with an offer: “If you ever want someone to give you a lot of money and screw everything up, we should talk.” (So far, Girls, which Apatow executive-produces and occasionally writes, has yet to make good on the doomed half of that promise.)

Then Apatow’s book brings in a new voice: Amy Schumer’s.

Schumer was a fan of his. Her own tone had been shaped by Knocked Up. “It had a huge effect on me when I saw it,” she says. “It was like, ‘Oh, you can make a comedy that’s hilarious, but have it be a beautiful story with some self-realization.’ ”

Apatow had been aware of the fast-
rising comedian as well — his comedy sensors are as finely tuned as military radar — but he found himself knocked sideways when he caught her hour-long interview with Howard Stern in the summer of 2012. Schumer was so quick, hilarious, and honest about her ex-boyfriends, current boyfriend, and outlook on life that when Apatow arrived at his destination, he stayed in the car and kept listening.

“She’s crazy funny. I mean, funny in a way that I can only really compare to Seth,” says Apatow of Schumer. As Rogen and Dunham know, when Apatow thinks you’re talented, he does something about it.

He invited Schumer to write him a script. Her first story was wild, high-
concept fiction — an idea both are keeping under wraps for now. It was good, but
Apatow wanted something more personal, the kind of movie Judd Apatow might have made if Judd Apatow had ever been a 33-year-old single woman.

As he saw it, Schumer’s debut film was her chance to define her screen identity. “It might be easier for Anne Hathaway to get great scripts,” Apatow notes. “But if you have a strong comic voice, there’s very few scripts that have your voice.”

Her second script became Trainwreck, Schumer’s semi-autobiographical comedy, due out in July, that gets real about her father with multiple sclerosis, her straight-as-an-arrow married younger sister, and her cynicism about love. There’s even a nod to the wrestler ex about whom Schumer opened up on Stern, here played by WWE’s John Cena.

“I’m an over-sharer by nature,” Schumer admits. “Judd and I aren’t afraid to go to the painful place. He knows when to gently nudge you to go there, to be like, ‘Why don’t you talk about how you really feel about your dad?’ ” She realized her dad’s shock illness had not only shaped her personal life, it had paved the way for the full-throttle fearlessness of her comedy career. “There’s no rhyme or reason to anything,” Schumer explains. “So you better just kick ass and do everything you can in your allotted time.”

On her Comedy Central show, Inside Amy Schumer, Schumer uses herself — her face, her body, her sexual appeal — to start a conversation about femininity. Self-mockery is a tool. “I think the idea that the show had a political philosophy snuck up on her,” Apatow observes. “Any time you write a sketch, you’re taking a position on something.”

But Trainwreck asked Schumer to do something more intimate: be vulnerable. The movie isn’t about all womankind; “it’s a look behind what makes somebody Amy,” Apatow says. He’d frequently check in to make sure she was comfortable putting her own life story on screen. Schumer always said yes. Even scenes that made her look awful, “If it was truthful, she was really into it,” Apatow says. “She was certainly braver than I would have been.”

Now he was the therapist. Of course, the irony about comedians turning their personal struggles into scripted entertainment is that the happy endings are only fictional. In This Is 40 and in Trainwreck, Apatow and Schumer confronted their real-life problems, with a catch. Apatow explains that, in his brand of filmmaking, he’s asking his subjects — including himself — how they might solve their own, real-life problems. “And usually in life you haven’t solved it — but for the movie you’re imagining mental health.”

“It was really hard,” Schumer adds. She realized, as Apatow did while making This Is 40, that telling your story also means taking on the guilt of revealing confidential things about your friends and family. That’s compounded when Trainwreck blurs fact and fiction, even in the characters’ names. In the film, Schumer is named Amy, her father, Gordon (Colin Quinn), is named Gordon, and her sister, Kim (Brie Larson), is named Kim. On days when Schumer had to shoot fights with Larson, she banned her actual sister, an associate producer on the film, from the set. “Those scenes were painful and heartbreaking,” she says. “If you’re doing your job, it feels like being trapped in a nightmare.”

Also, just as her onscreen attempts at a tentative romance with a surgeon (Bill Hader) force her character to learn to trust, Schumer’s creative partnership with Apatow pushed her to do something scary: allow someone to help take care of her.

“On my TV show, I have the final say on everything. In my stand-up, I’ve got no one, no boss,” Schumer says. “So trusting him was a constant exercise, and he was very patient with me.” During sleepless nights, she’d fire off frantic emails cross-checking that they weren’t reducing her character to a slut or a drunk.

For Apatow, it was easier to “till someone else’s soil,” as he recently put it on Pete Holmes’s podcast You Made It Weird, than to continue plowing his own life for material. “I think from working with Lena, I thought I could understand Amy,” he says. “And Amy’s playing someone who’s in her early thirties, so in a way it’s a story that
almost begins where Girls ends.”

Initially he just wanted to guide Schumer through the process of getting her first film made. He wasn’t planning to direct Trainwreck himself. He’s never
directed anyone else’s script. Yet slowly
he realized that, unlike Bridesmaids and Superbad, he didn’t want to hand over Schumer’s story to another director. That is, if Schumer was game. Says Apatow, “I didn’t want to force myself on her!”

Now Schumer is in Apatow’s expanded family portrait, alongside Dunham and the cast of Bridesmaids.

“She’s a great voice for ‘Fuck you, I want to say this!’ ” Apatow says. “I think you can almost see the progression of Tina and Amy and Mindy and Lena and Amy now — that first Amy is Poehler.”

While it might seem odd that Apatow, the man who popularized man-children, is one of the driving forces behind the new surge of female-driven comedies, his celebration of strong, fascinating woman is nothing new.

Apatow himself hasn’t changed — he’s just never gotten enough credit for being a feminist.

“I loved Gilda Radner as much as I loved Bill Murray, as a kid,” he says. “I didn’t understand there was a difference between them.” The comedian who first inspired a nine-year-old Apatow to take the stage was a one-legged woman in a wheelchair: Totie Fields. At 22, he was writing jokes for Roseanne and learning about stretch marks. At home, his world is ruled by Venus. He’s had almost two decades of marriage to grumble about the bad roles that get sent to his wife, and now that his lovely daughters are old enough to be into makeup, he reminds them that a personality matters more than being pretty.

Apatow attacks misogyny, even when it comes from the comedy legends who shaped him. At times, his entire Twitter feed is a one-man assault on Bill Cosby (“He’s clearly insane”), whose records spun through his childhood. And when Jerry Lewis said that he preferred to think of women as “a producing machine that brings babies in the world,” Apatow took the stage at the Critics’ Choice Awards and groaned, “I’d like to say, with all respect, fuck you.”

On the surface, Knocked Up and The 40-Year-Old Virgin look like celebrations of immaturity. But Apatow is more interested in turning his boys into men. (“It would be weird if the first movie I wrote was all about the issues of a woman, because I’m a young idiot,” Apatow says of his first four films.) His heroes grow up, even if that means growing past their idiot friends. In a city that celebrates eternal youth, he doesn’t identify with the Peter Pans. He wed one of his first serious girlfriends, quickly had children, and settled into domesticity. As he confessed to the Hollywood Reporter, “I had zero wild years. I had a wild week, maybe.”

He adds, “It takes decades of being married and having two daughters and
being around a lot of women to begin to understand 1 percent of what their perspective is.”

In college, Dunham bought into the outcry that Knocked Up was sexist for making Katherine Heigl’s character a humorless shrew. As she told GQ in 2013, “It was what was cool to do, just like I was always doing sit-ins for causes I didn’t understand.” Today, after four years of late-night Skype calls with Apatow and conversations about their insecurities, she sticks up for her producer, writer, and friend.

“He’s this incredibly sensitive, emotional creature whose comedy is always,
at its root, about love and all its complexities,” Dunham says. “Judd roots for humanity, for romance, for the idea that people can grow and change.”

Including himself. His fear of failure is the flip side of his quest for self-improvement: to do more, say more, give more. Over the last six months, Apatow has hosted benefits for autism, the Wounded Warrior Project, mental health, Nepal,
Alzheimer’s, epidermolysis bullosa, Haiti, two pediatric cancer charities, literacy, gun-violence prevention, a children’s hospital, and the David Lynch Foundation for Consciousness-Based Education and World Peace, whose goal is to teach transcendental meditation to at-risk high schoolers. Apatow knows firsthand that money, even a small amount, can change a life — say, the $6,000 bill that got him booted from USC.

“I was making burritos, praying that somehow I would have enough money that I wouldn’t get kicked out,” Apatow recalls. “And then one day they knocked on the door and said, ‘OK, you’re done.’ ”

Comedians have been neurotic ever since Woody Allen wooed Annie Hall. But Apatow is different. His movies — and his life — are about more than winning the girl. They’re about how you become a good person (a question Allen never bothers to ask).

A Judd Apatow movie is nice. And in today’s culture, where cruelty reigns even in comedy, Apatow’s insistence that everyone has feelings and no one is a villain is quietly revolutionary — especially given that he won’t paste on false happy endings. As Heigl says in Knocked Up, “Just because we’re two nice people doesn’t mean we should stay together.”

What’s fascinating about Apatow is his urge to make the real world as nice as his movies. He wants to believe that good guys win. “I’m always drawn to these people that are very hungry, ready, and nice,” he says. Which is why when he meets one, he does everything he can to help.

Take the Lonely Island musical comedy trio of Andy Samberg, Akiva Schaffer, and Jorma Taccone. Apatow is so bullish about their talent that when he guest-edited the December 2012 issue of Vanity Fair, he asked them in print to give him a call — and, as if to call his own bluff, published his phone number. “It was the real line to Apatow Productions,” Schaffer recalls. The four are now working on Lonely Island’s first feature, a mockumentary on the modern Bieberian pop star.

Or Paul Reubens, whose plans for another Pee-wee Herman film didn’t gel until Apatow came to see his live show and laughed his head off. Reubens admits, “I’m not the most trusting person” — especially when protecting his signature persona. But when the two met, Apatow brought a Polaroid picture he’d snapped in 1983, when he was still in high school, of Pee-wee at a comedy club. “That just floors me every time I think of it,” Reubens says. He decided to take a leap of faith and allow Apatow to produce the first Pee-wee film in 27 years, Pee-wee’s Big Holiday, out this December.

“My friends were immediately like, ‘Judd Apatow’s producing your movie? How does that work?’ ” Reubens says. But Apatow earned Reubens’s trust by fighting to make sure that the film feels like a Pee-wee Herman film. “You’re making a movie with a great big guardian angel on your shoulder,” Reubens says. “I wouldn’t have made this movie without him.”

Then there’s Paul Rust, a talented UCB comic whom Apatow tapped to co-write the Pee-wee Herman movie and then teamed with to produce Love, a TV show based on Rust’s romance with his fiancée, Lesley Arfin, a former comedy writer on Girls and Brooklyn Nine-Nine. (Netflix has already green-lit the first two seasons, a show of confidence it’s bestowed only on House of Cards.)

“When we sold the show, I told him how much it meant to be a part of somebody who’s trying to put out in the world that it’s OK to be kind to people, and it’s OK to be thoughtful and present,” Rust says. “That message isn’t usually put out there. I don’t know anybody else who’s expressing it in studio comedies. I feel like he’s carrying the torch for Nineties independent films in a 21st-century studio world.”

Rust points to This Is 40, where Rudd, Apatow’s onscreen counterpart, runs a record label that lavishes effort on the underdogs he alone believes in. Says Rust, “It’s like, ‘Oh, that’s what Judd’s doing with comedy.’ ”

Today, Apatow is in production and pre-production and promoting more than a half-dozen projects. In one day, Apatow can toggle between Pee-wee slapstick, Lonely Island ballads, the sweetness of Love, the unsparing scrutiny of Girls and Schumer, and the crowd-pleasing hijinks of Bad Moms, his and his wife’s newest project, whose Bridesmaids-like pitch
triggered an international bidding war at Cannes. His family tree continues to grow. He’s been meeting more and more with his new favorites — Pete Davidson, Pete Holmes, Jemaine Clement, Kumail Nanjiani — and, in the true sign of a busy man, is mimicking Steve Jobs by adopting a no-fuss uniform: a black polo shirt.

In the years since Freaks and Geeks and Undeclared were canceled, the TV landscape has changed. Apatow has happily discovered that now there’s room for creators like him to take risks. “Freaks and Geeks got canceled because it only had 7 million viewers,” he says. “That’s more than Girls has right now. You can have a niche audience and survive.” He laughs. “I’m trying to trick myself into feeling less pressure.”

Instead of writing his next script, Apatow is going back to his first comedy obsession: the microphone. He’d prodded Schumer to make a movie. Schumer elbowed him to reclaim the stage he quit 25 years ago. Why not return to where his love of comedy began?

During Trainwreck‘s four-month New York shoot, every night he’d call “cut” around 8 p.m., jump into a car, and ride to the Comedy Cellar to do a stand-up set. Young Judd would’ve panicked at going on sandwiched between Andrew Dice Clay and Louis C.K. Older Judd was
finally able to relax. Even if he wasn’t as good as the rest of the acts, “I would have nights where I was semi-charming.

“I wasn’t that great at doing it when I was young, because I didn’t have that much to say,” he continues. “To come back and do it at 47, I have a lot more stories and ideas. And I don’t have to be terrified that if it goes badly, I won’t eat.”

If he’s temporarily run out of life events for a full movie, he’s bursting with zingers for the stage — so many that at the end of a hysterical 75-minute set at Largo, Apatow literally pulled his joke ideas from a bucket. He riffed on everything: his mother’s refusal to breast-feed him, his weight, the two times he’s met Obama, “dad bod,” his paranoia that David Schwimmer hates him, and his therapist’s revelation that he used to treat O.J. Simpson. “So I go, ‘Oh, you’re the worst therapist ever,’ ” he cracks. Apatow’s common theme is, as ever, his own insecurity. But onstage he has no reason to be insecure. He kills.

“I didn’t like not being thought of as a comedian,” he admits. “A friend of mine said, ‘Why would you do that? You’re a
director.’ I’d rather be thought of as a
comedian than a director.”

It makes sense that Apatow might be most happy holding a mic. To get honest in This Is 40, he had to write a script, raise $35 million, hire hundreds of people, work for over a year, put his loved ones in emotional jeopardy, and hold his breath to find out if his struggle was worth it.

“There’s so much pressure when you’re making movies, and then maybe when it comes out you have a moment of joy — or humiliation, if no one else likes it,” Apatow says. But stand-up is simple and immediate. He speaks. And the audience either stares back or laughs. Apatow smiles. “The laughter’s what tells you that everything is going to be OK.”